ON EMBARRASSING MOMENTS… With Dan Levy and Phoebe Waller-Bridge

Summary

Podcast Summary

Podcast: How To Fail With Elizabeth Day
Episode: ON EMBARRASSING MOMENTS… With Dan Levy and Phoebe Waller-Bridge
Date: November 3, 2025
Host: Elizabeth Day
Guests: Phoebe Waller-Bridge, Dan Levy

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Episode Overview

This special archive episode dives into the theme of public humiliation and embarrassing moments, revisiting two of the podcast’s most beloved and hilarious stories. Host Elizabeth Day brings back viral tales from writer-actress Phoebe Waller-Bridge and actor-writer Dan Levy, exploring what these embarrassing failures taught them about self-acceptance, humor, and personal growth. The episode maintains a comedic, honest tone, celebrating vulnerability and learning through shared human awkwardness.

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Key Discussion Points & Insights

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1. Phoebe Waller-Bridge and the Apple Crumble Incident

[02:55 – 05:55]

• Setting the Scene: During filming of The Iron Lady, Phoebe was starstruck working with Meryl Streep, who was in full prosthetic makeup and remained largely silent and focused on set.

  • Phoebe confesses:
    "I go weird around celebrities and always very in a very individual way for each celebrity. I should just not be around them." [02:55]

• The Moment: One day, Meryl breaks character and, in her Margaret Thatcher voice, asks the room how everyone’s day is going, surprising the cast and crew.

• Phoebe’s Triumph & Downfall:

  • Phoebe manages to make Meryl laugh with a joke and feels triumphant:
    "And everyone else looked at me with such steel and an ashen face and fury. And I was like, I've won it. She's mine." [04:11]
  • Later, at lunch, Meryl approaches Phoebe, who is eating apple crumble, and asks what she's eating.
  • Overexcited, Phoebe flings the pudding all over herself:
    "I flung my apple crumble straight into my chest, my costume chest." [05:01]
  • Meryl assures her, “I wasn’t gonna take it from you,” before walking away, leaving Phoebe mortified, clutching messy apple crumble to her silk shirt.

• Memorable Quote:
  Phoebe Waller-Bridge:

  "I literally squawked my apple crumble. And she went, 'Oh.' And then she went back into her American accent, which she hadn't done for the whole time, and she went, 'I wasn't gonna take it from you.'" [05:04]

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2. Dan Levy and the Birthday Cake Disaster

[06:10 – 09:13]

• Childhood Humiliation: Dan recounts a vivid memory from second grade (age 7-8) in Canada, when his mother brought in a belated birthday cake for him to share at school.
• The Mishap:
  • Overzealous to impress his classmates and teacher, Dan rushes to carry the cake himself.
  • He trips and the cake falls onto his shoes and the floor. The class erupts in laughter.
  • Flustered and panicked, he begins to eat cake off his shoes—a spontaneous, embarrassed reaction.
  • The moment lingers in his memory, representing not just physical but emotional awkwardness.
  • Dan reflects:
    "It was the deepest humiliation I'd felt in my young life. And I looked around and didn't know what to do...my reaction was to sort of, I guess, go completely pale in the face and then reach down and start to eat the cake off my shoes." [07:40]
• Insight: This event, for Dan, marks an early feeling of overreaching (hubris) and failing publicly, sticking with him ever since.
• Reflection on School: Both Dan and Elizabeth discuss the difficulties of school as an environment for those hiding their true selves and the lasting impact of childhood embarrassment.
  • Dan:
    "I've never liked school. Not a single day. And I think part of it had to do with the fact that I wasn't the truest expression of myself." [09:13]

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3. Coping with Failure, Laughter, and Control

[09:17 – 11:19]

• Turning Humiliation into Humor:
  • Elizabeth notes the repeated theme of childhood embarrassment and its powerful, formative nature.
  • She observes that being laughed at often propels people to seek control over comedic moments later in life—as writers, comedians, or performers.
  • Dan agrees:
    "Of course you want to be in control of when people laugh."
• Comedic Ethics:
  • Dan shares a guiding principle learned from his father and Catherine O'Hara:
    "You can tell very funny jokes about people in celebration of people, but not at their expense. And there's a very fine line between cruel comedy and observational comedy. And I will always lean towards observational comedy." [10:11]
  • He regards the warmth and inclusivity of Schitt’s Creek as the model for comedic storytelling:
    "There was a kind of democracy of comedy across the board. There was no butt of the joke."

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Most Memorable Quotes

• Phoebe Waller-Bridge:

  "I just got so excited about the banter with Meryl that I flung my apple crumble straight into my chest, my costume chest." [05:00]

• Meryl Streep (quoted by Phoebe):

  "I wasn't gonna take it from you." [05:09]

• Dan Levy:

  "My reaction was to sort of, I guess, go completely pale in the face and then reach down and start to eat the cake off my shoes. I don't know what that impulse was." [07:45]

• Dan Levy:

  "You can tell very funny jokes about people in celebration of people, but not at their expense." [10:11]

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Important Timestamps

• [02:55] Phoebe's apple crumble, Meryl Streep story begins
• [05:00] Phoebe accidentally spills apple crumble all over herself
• [06:10] Dan introduces his second-grade birthday cake humiliation
• [07:45] Dan eats cake off his shoes in a panic
• [09:13] Dan on not enjoying school and hiding his true self
• [10:11] Dan’s philosophy on comedy and jokes

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Conclusion

Elizabeth Day’s collection of joyous, honest failures affirms the deeply human experience of social awkwardness and mortification—showing how humor and vulnerability can ultimately connect us, teach us, and empower us to tell our own story. The episode ends with an encouragement to share failures, reminding listeners that “a fail shared is a fail halved.”

Transcript

[Loose Women Host]

The Loose Women podcast is back, and this time we've shaken things up a bit. In Loose Women Just Between Us, we'll be asking you to send in your juicy problems and dilemmas for our consideration. Then every week you get two of your favorite Loose Women or us.

[Elizabeth Day]

And what we will try and do is help you solve your problems just.

[Loose Women Host]

By drawing on our own life experience.

[Elizabeth Day]

And there's a lot.

[Loose Women Host]

So why don't you come and join us? Just search Loose Women Just between us, wherever you're listening to this podcast.

[Jonathan Van Ness]

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[Elizabeth Day]

Welcome back to this week's archive episode, reflecting on some of the best bits from how to Fail's past. This week, we're keeping it light and taking a look at some of the funniest and most entertaining embarrassing moments from guests on how to Fail, starting with the one and only Phoebe Waller Bridge. This is honestly one of the most hilarious moments. Listening back to Phoebe talking about trying to impress Meryl Streep and her body sort of malfunctioning. And all I need to tell you, because you might have heard it before, is that it involves an apple crumble. I've lost count of the number of times listeners have come up to me at live shows and said that apple crumble story, and I know immediately what they're talking about. It's one of those anecdotes that gets better every. Every time you hear it. Then Dan Levy Talks about a birthday cake failure he remembers vividly from his childhood and the humiliation he felt at his knee jerk response to dropping it. I hope this episode brings some light to your day and reminds you that we all have embarrassing moments, whoever you are. First, it's Phoebe and the apple crumble.

[Phoebe Waller-Bridge]

I was really excited to meet Meryl Streep when I was doing the Iron Lady. Although she. I was weird with her, though. I go weird around celebrities and always very in a very individual way for each celebrity. I should just not be around them.

[Elizabeth Day]

What did you say to Meryl Streep that was weird?

[Phoebe Waller-Bridge]

Well, Meryl Streep was doing the Iron lady and she was in this prosthetic sort of whole body face scenario. The lights were so hot. So whenever she was on set, she couldn't really speak in between because so much energy was taken up and just like, acting through this, you know, mask and everything. So when the light. So she would never say anything in between cuts. And we always knew it. She was always like, I'm really sorry, but I just can't. I knew I just need to, like, power down, have a glass of, like, sip some water through the straw. But there was one day when the lights went off, they called cut. And then she just turned around to this room of people and went, you know, in her Margaret Thatcher voice and just went, hey, now, how's everybody's day? And everyone just freaked out. Everyone's like froze in the room because they were like, oh, my God, everyone. At the same time, like, we were like vultures. Just like, this is our moment to have to share words with Meryl Streep. And so everyone sort of was being very casual and it was that the scene was like a drinks party or something, but edging towards her with this kind of wild look in their eye. And everyone was trying to have some personal bants with Meza. So she was just opening the conversation. And then it was getting, like, really competitive and we were like, crowding around her, but everyone was trying to be very casual. And then she started up this conversation about something. Anyway, I tried a joke and it landed and she laughed and she was like, oh. And everyone else looked at me with so steel and an ashen face and fury. And I was like, I've won it. She's mine. She's mine. So she was mine. But after that, I was like, she's totally mine. She's totally mine. We're gonna have a day together. We're gonna, like, like, nod to each other respectfully in the corridors. We're gonna. We may even, like, you know, graduate to a drink at some point. And then at lunchtime, I was sitting at this table with everybody and I was eating this apple crumble. And she came down the stairs. She was feeling lively this day, obviously, outside of the prosthetic. She came down the stairs and. And she was walking towards me and I was like, oh, my God. Oh, my God. Like, she's going to come to the table and we're friends now, because I was the one that made her laugh. And she walked up to the table and she put her hand on my shoulder and she said, oh, what are you eating? I'll never answer my dis. I got so excited about the banter with Meryl that I flung my apple crumble straight into my chest, my costume chest. And I. And I literally squawked my apple crumble. And she went, oh. And then she went back into her American accent, which she hadn't done for the whole time, and she went, I wasn't gonna take it from you. And I was just holding this awful, like, dripping pudding over my. My beautiful silk shirt. And I'm just holding it there really tightly, not letting it go. I was just like, oh, my gosh. My God. Everyone stood like, what was that? That was the strangest response. And then she was like, okay. And then she. She moved off and then I had to go and apologise. Costume thing. So just weird stuff like that.

[Elizabeth Day]

You made her break character. You made Meryl Streep break character. Your first failure relates to a time in second grade, which for UK listeners, is when you're about seven or eight.

[Dan Levy]

Years old, I would think so, yeah. It's like kindergarten for a couple years and then first grade and second grade. So I don't know what that is.

[Elizabeth Day]

So what happened?

[Dan Levy]

I bring this up as a failure because sometimes, you know, there are these snags in our memory where we stick on these moments and they should have just come and gone, and yet they are as vivid as the day it happened. And the earliest huge failure for me was it was my birthday. Except my birthday's in August. So we. You know, you're very young and you want to celebrate with everybody because everybody who has a birthday during the school year gets to have cake and thing. So my mom made me a cake to bring in right as the school year started in September in Canada. So we did a celebration around my birthday because it's in August, and I was feeling a little embarrassed anyway because it wasn't really my birthday, but it Was. Anyway, the cake is at the back of the classroom. My teacher says, we have a surprise for the class. I knew what the surprise was. And she said, daniel, I'm gonna go and get the cake. And I said, no, no, no, I can get the cake. I'll get the cake. Very excited, happy to share with the class. The cake is revealed. The class is excited. Just as I get to the front of the classroom, I trip, and the cake falls out of my hand and onto my shoes and flips sort of cake first onto the ground. And the class, obviously is hysterically laughing. And it is the deepest humiliation I'd felt in my young life. And I looked around and didn't know what to do. And it's that time where you're young and you don't know whether you should cry or laugh. And so my reaction was to sort of, I guess, go completely pale in the face and then reach down and start to eat the cake off my shoes. I don't know what that impulse was. I think it was kind of panic and deep embarrassment. And it was a moment that. That I've remembered because in a way, I've kind of intellectualized it as, like, the first exertion of hubris or something. Like, I was like, no, no, no, I got the cake. You don't need to get the cake for me. I have it. And I didn't. I was too young, My hands were probably too small, the cake was too heavy, all of those things. And then just. It was a.

[Jonathan Van Ness]

It was.

[Dan Levy]

It was a symbolic thing.

[Elizabeth Day]

I have to say, it's so interesting to me how many people on this podcast do choose moments like that from their early childhood where they embarrass themselves. And I think it's that thing of when you're a child and you're trying to work out who you are in this confusing world, and you don't know whether someone is making fun of you or is on your side. It can feel quite terrifying.

[Dan Levy]

Yeah.

[Elizabeth Day]

And I. A bit like you. I didn't have the happiest school experience for various reasons. And I wonder what you were like after that as a child at school. What was your school experience?

[Dan Levy]

I just. To me, I look back, I've never liked school.

[Elizabeth Day]

Me neither.

[Dan Levy]

Not a single day. And I think part of it had to do with the fact that I wasn't the truest expression of myself. And I think when you're playing a part, it gets exhausting. And you don't like yourself because you're hiding yourself. In my particular case, I just wanted to get through it because I think in my mind I thought once school is done, people will have the maturity to accept me. I think it was toward the end of the last year of my high school experience that I told some friends it wasn't a safe space. It's.

[Phoebe Waller-Bridge]

Tough.

[Elizabeth Day]

It's tough. And I think also when you're the butt of the joke or you are bullied, it makes sense to me that you now write the jokes. Of course you want to be in control of when people laugh.

[Dan Levy]

Yeah, I didn't think of it that way, but now that you bring it up, it makes sense.

[Elizabeth Day]

Yeah.

[Dan Levy]

And also. Yeah, a control of and also how the jokes are formed. And I think the one thing I learned from both my dad and Catherine o' Hara during the creation of Schitt's Creek was you can tell very funny jokes about people in celebration of people, but not at their expense. And there's a very fine line between cruel comedy and observational comedy. And I will always lean towards observational comedy. The roast sort of world of it all is its own subculture, which is something I would kill for the self confidence to endure. I also think that's why shits worked. Yes, because there was a warmth to the comedy and everyone was laughing at themselves as well as everyone else. There was a kind of democracy of comedy across the board. There was no butt of the joke. And that will always be something I'm trying to rewrite through my whole life. I think through anything I do is the kind of reversal of the first chapter of of my own life, I guess.

[Elizabeth Day]

Please do follow how to fail to get new episodes as they land on Apple Podcasts, Spotify, Amazon Music, or wherever you get your podcasts. Please tell all your friends this is an Elizabeth Day and Sony Music Entertainment original podcast. Thank you so much for listening.

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[Phoebe Waller-Bridge]

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